195705-40-9Relevant academic research and scientific papers
Synthesis and conformation of 3′,4′-BNA monomers, 3′-O,4′-C-methyleneribonucleosides
Obika, Satoshi,Morio, Ken-Ichiro,Nanbu, Daishu,Hari, Yoshiyuki,Itoh, Hiromi,Imanishi, Takeshi
, p. 3039 - 3049 (2007/10/03)
In order to develop novel 2′,5′-linked oligonucleotide analogues aimed for antivirus reagents and antisense/antigene oligonucleotides, novel nucleoside analogues, 3′-O,4′-C-methyleneribonucleosides (3′,4′-BNA monomers) were synthesized via two synthetic routes. The first route starting from uridine utilized a regioselective ring-closure reaction of the 4′-C-(p-toluenesulfonyl)oxymethyluridine derivative. The second route involved a coupling reaction of 1,2,3-tri-O-acetyl-4-C-(p-toluenesulfonyl)oxymethylribofuranose derivative with nucleobases followed by oxetan-ring formation to afford the 3′,4′-BNA monomers bearing all four nucleobases. By means of 1H NMR, X-ray crystallography and computational analysis, the sugar puckering of the 3′,4′-BNA monomers was found to be restricted in S-conformation (C1′-exo-C2′-endo puckering mode).
Synthesis and conformation of 3′-O,4′-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2′,5′-linked oligonucleotide modification
Obika, Satoshi,Morio, Ken-Ichiro,Nanbu, Daishu,Imanishi, Takeshi
, p. 1643 - 1644 (2007/10/03)
Novel bicyclic nucleoside analogues 3′-O,4′-C-methylene-ribonucleosides 1 are conveniently prepared starting from uridine; the sugar puckering of 1 is found to be nearly in the S-conformation by means of PM3 calculations and 1H NMR studies.
